Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 13, Pages 3496-3499Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201311105
Keywords
CH activation; copper; cyclization; heterocycles; lactams
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Funding
- ERATO from JST
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The first copper-catalyzed intramolecular C(sp(3))H and C(sp(2))H oxidative amidation has been developed. Using a Cu(OAc)(2) catalyst and an Ag2CO3 oxidant in dichloroethane solvent, C(sp(3))H amidation proceeded at a terminal methyl group, as well as at the internal benzylic position of an alkyl chain. This reaction has a broad substrate scope, and various -lactams were obtained in excellent yield, even on gram scale. Use of CuCl2 and Ag2CO3 under an O-2 atmosphere in dimethyl sulfoxide, however, leads to 2-indolinone selectively by C(sp(2))H amidation. Kinetic isotope effect (KIE) studies indicated that CH bond activation is the rate-determining step. The 5-methoxyquinolyl directing group could be removed by oxidation.
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